4.8 Article

Regioselective Catalytic Hydroboration of Propargylic Species Using Cu(I)-NHC Complexes

Journal

ORGANIC LETTERS
Volume 14, Issue 18, Pages 4790-4793

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol302086v

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Funding

  1. NSF [CHE-0809261, 1152020]
  2. Pfizer
  3. Corning Glass
  4. FSU
  5. Direct For Mathematical & Physical Scien
  6. Division Of Chemistry [1152020] Funding Source: National Science Foundation

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The catalytic regioselective hydroboration of propargylic alcohols and ethers was investigated using NHC-CuCl. We observe that different NHC-CuCl complexes catalyze hydroborations of propargylic substrates with opposite regioselectivity. A 6-NHC-CuCl complex provides alpha-selectivity whereas beta-selectivity is achieved using a 5-NHC-CuCl complex. The reaction tolerates a wide range of functional groups.

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